3-Quinuclidone

3-Quinuclidone
Names
	Preferred IUPAC name 1-Azabicyclo[2.2.2]octan-3-one
Identifiers
CAS Number	3731-38-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL377716;
ChemSpider	18381;
ECHA InfoCard	100.020.989
EC Number	223-087-9;
PubChem CID	19507;
UNII	P4VF4G5PTA;
CompTox Dashboard (EPA)	DTXSID0063151 ;
	InChI InChI=1S/C7H11NO/c9-7-5-8-3-1-6(7)2-4-8/h6H,1-5H2 Key: ZKMZPXWMMSBLNO-UHFFFAOYSA-N;
	SMILES C1CN2CCC1C(=O)C2;
Properties
Chemical formula	C7H11NO
Molar mass	125.171 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H411
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Quinuclidinone is a bicyclic organic compounds with chemical formula HC(C₂H₄)₂(C(O)CH₂)N. Its basicity is indicated by the pKa of the conjugate acid, which is 7.2. In contrast quinuclidine is about 100x more basic.^[2]

Synthesis and reactions

Its hydrochloride salt can be synthesized by a Dieckman condensation:^[3] It is a precursor to quinuclidine.

Organic reduction of 3-quinuclidone gives the compound quinuclidine, structurally related to DABCO, which has one additional bridgehead nitrogen atom.

References

↑ "Quinuclidin-3-one". pubchem.ncbi.nlm.nih.gov.
↑ Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y. (2003). "Correlation between pKa and Reactivity of Quinuclidine-Based Catalysts in the Baylis−Hillman Reaction: Discovery of Quinuclidine as Optimum Catalyst Leading to Substantial Enhancement of Scope". The Journal of Organic Chemistry. 68 (3): 692–700. doi:10.1021/jo026671s. PMID 12558387.
↑ H. U. Daeniker, C. A. Grob (1964). "3-Quinuclidone Hydrochloride". Organic Syntheses. 44: 86. doi:10.15227/orgsyn.044.0086.

[1] "Quinuclidin-3-one". pubchem.ncbi.nlm.nih.gov.

[2] Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y. (2003). "Correlation between pKa and Reactivity of Quinuclidine-Based Catalysts in the Baylis−Hillman Reaction: Discovery of Quinuclidine as Optimum Catalyst Leading to Substantial Enhancement of Scope". The Journal of Organic Chemistry. 68 (3): 692–700. doi:10.1021/jo026671s. PMID 12558387.

[3] H. U. Daeniker, C. A. Grob (1964). "3-Quinuclidone Hydrochloride". Organic Syntheses. 44: 86. doi:10.15227/orgsyn.044.0086.

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Synthesis and reactions

References